Structural Elucidation of Tenebrathin: Cytotoxic C-5-Substituted γ-Pyrone with a Nitroaryl Side Chain from Streptoalloteichus tenebrarius

Shotaro Hoshino; Takaaki Mitsuhashi; Takashi Kikuchi; Chin Piow Wong; Hiroyuki Morita; Takayoshi Awakawa; Makoto Fujita; Ikuro Abe

doi:10.1021/acs.orglett.9b02443

Structural Elucidation of Tenebrathin: Cytotoxic C-5-Substituted γ-Pyrone with a Nitroaryl Side Chain from Streptoalloteichus tenebrarius

Shotaro Hoshino, Takaaki Mitsuhashi, Takashi Kikuchi, Chin Piow Wong, Hiroyuki Morita, Takayoshi Awakawa, Makoto Fujita, Ikuro Abe^*

^*この論文の責任著者

和漢医薬学総合研究所研究開発部門資源開発分野（天然物創薬学領域）

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

10 被引用数 (Scopus)

抄録

Tenebrathin (1), a new C-5-substituted γ-pyrone with a nitroaryl side chain, was isolated from the rare actinomycete Streptoalloteichus tenebrarius NBRC 16177. The chemical structure of 1 was elucidated by a spectroscopic analysis using the crystalline sponge method of crystallization-free X-ray crystallography. The biosynthetic origin of the unusual C-5-substituted γ-pyrone in 1 was revealed by a ¹³C-labeling experiment. Compound 1 exhibited moderate cytotoxicity against several cancer cell lines and likely targets some protein kinases.

本文言語	英語
ページ（範囲）	6519-6522
ページ数	4
ジャーナル	Organic Letters
巻	21
号	16
DOI	https://doi.org/10.1021/acs.orglett.9b02443
出版ステータス	出版済み - 2019/08/16

ASJC Scopus 主題領域

生化学
物理化学および理論化学
有機化学

UN SDG

この成果は、次の持続可能な開発目標に貢献しています

文献へのアクセス

10.1021/acs.orglett.9b02443

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引用スタイル

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abstract = "Tenebrathin (1), a new C-5-substituted γ-pyrone with a nitroaryl side chain, was isolated from the rare actinomycete Streptoalloteichus tenebrarius NBRC 16177. The chemical structure of 1 was elucidated by a spectroscopic analysis using the crystalline sponge method of crystallization-free X-ray crystallography. The biosynthetic origin of the unusual C-5-substituted γ-pyrone in 1 was revealed by a 13C-labeling experiment. Compound 1 exhibited moderate cytotoxicity against several cancer cell lines and likely targets some protein kinases.",

author = "Shotaro Hoshino and Takaaki Mitsuhashi and Takashi Kikuchi and Wong, {Chin Piow} and Hiroyuki Morita and Takayoshi Awakawa and Makoto Fujita and Ikuro Abe",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b02443",

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T2 - Cytotoxic C-5-Substituted γ-Pyrone with a Nitroaryl Side Chain from Streptoalloteichus tenebrarius

AU - Hoshino, Shotaro

AU - Mitsuhashi, Takaaki

AU - Kikuchi, Takashi

AU - Wong, Chin Piow

AU - Morita, Hiroyuki

AU - Awakawa, Takayoshi

AU - Fujita, Makoto

AU - Abe, Ikuro

PY - 2019/8/16

Y1 - 2019/8/16

N2 - Tenebrathin (1), a new C-5-substituted γ-pyrone with a nitroaryl side chain, was isolated from the rare actinomycete Streptoalloteichus tenebrarius NBRC 16177. The chemical structure of 1 was elucidated by a spectroscopic analysis using the crystalline sponge method of crystallization-free X-ray crystallography. The biosynthetic origin of the unusual C-5-substituted γ-pyrone in 1 was revealed by a 13C-labeling experiment. Compound 1 exhibited moderate cytotoxicity against several cancer cell lines and likely targets some protein kinases.

AB - Tenebrathin (1), a new C-5-substituted γ-pyrone with a nitroaryl side chain, was isolated from the rare actinomycete Streptoalloteichus tenebrarius NBRC 16177. The chemical structure of 1 was elucidated by a spectroscopic analysis using the crystalline sponge method of crystallization-free X-ray crystallography. The biosynthetic origin of the unusual C-5-substituted γ-pyrone in 1 was revealed by a 13C-labeling experiment. Compound 1 exhibited moderate cytotoxicity against several cancer cell lines and likely targets some protein kinases.

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